Sodium Hydroxide → 4-Amino-6-bromo-3-methoxypyridine-2-carboxylic acid

HRID 378791Notes

Reaction equation

HRID 378791 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Br:8])[N:5]=[C:4]([C:9]([O:11]C)=[O:10])[C:3]=1[O:13][CH3:14].[OH-].[Na+]>CO>[NH2:1][C:2]1[CH:7]=[C:6]([Br:8])[N:5]=[C:4]([C:9]([OH:11])=[O:10])[C:3]=1[O:13][CH3:14]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21696668Methyl 4-amino-6-bromo-3-methoxypicolinate

Product 1

HCID 216966194-Amino-6-bromo-3-methoxypyridine-2-carboxylic acidYield 63.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To methyl 4-amino-6-bromo-3-methoxypyridine-2-carboxylate (0.300 g, 1.15 mmol) in 10 mL of methanol was added 1N NaOH (1.15 mL, 1.15 mmol). The reaction mixture was stirred at room temperature for 1 hr and concentrated to dryness in vacuo. Diethyl ether and H2O were added. The aqueous layer was acidified with 1N HCl until pH=2 and concentrated to dryness. Methanol (50 mL) was added to the white solid. The mixture was filtered and the filtrate concentrated to dryness. Triturating with 5% diethyl ether/pet ether gave 0.180 g of a light pink solid. 1H NMR(DMSO): δ 3.60 (s, 3H); 6.80 (S, 1H).

Workup

  1. concentrationconcentrated to dryness in vacuo
  2. additionDiethyl ether and H2O were added
  3. concentrationconcentrated to dryness
  4. additionMethanol (50 mL) was added to the white solid
  5. filtrationThe mixture was filtered
  6. concentrationthe filtrate concentrated to dryness
  7. customTriturating with 5% diethyl ether/pet ether

Sources & evidence

ORD record
ord-87a271092ade4526bb8104573ff2a641
Source dataset
uspto-grants-2001_10
Patent number
US06297197B1

Reaction notes

Loading…